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Key Concepts of Mishlei 14-08 (Shrewdness)
The wise person is mentally alert and his mind is involved in proactive thought processes. Thus, he considers what may reasonably be expected to happen under present conditions and how conditions are likely to change. He also considers what options are open to him, evaluating each option and making a judgment of what is likely to result with each course of action. Having considered all this he carefully chooses the wisest course of action.
The mental quality that enables a person to maintain this kind of mental alertness is referred to as shrewdness. The shrewd person does not have a passive attitude, simply accepting things as they are. Instead he looks beyond surface appearances and he is continually questioning himself to be sure that he is doing the right thing.
Of course, the same quality of shrewdness has a negative potential if used unwisely. The foolish person can use his mental alertness to take advantage of others, developing sophisticated schemes to deceive people and manipulate events to suit his interests. He may think he is acting wisely, but actually he is a fool, because he is only harming himself.
In the Torah, shrewdness is referred to by the word עָרוּם and the serpent ( נָחָשׁ ) that introduced evil to mankind (Bereishis 3:1) is characterized by this word. When man emulates the נָחָשׁ to practice deception, he is a fool. Instead it is his duty to use the quality of shrewdness as a means to identify and resist evil.
Exploring Mishlei
(ח) חָכְמַת עָרוּם הָבִין דַּרְכּוֹ וְאִוֶּלֶת כְּסִילִים מִרְמָה:
With the wisdom of the shrewd man, he understands his way but the foolishness of fools [results in] deceit.
This proverb contrasts the positive and negative uses of shrewdness. When used by a wise man, shrewdness enables him to understand the right choices to make in life. When used by a fool, shrewdness becomes a foolish quality which provides the illusion of advantage, but ultimately is harmful to the practitioner.
Learning Mishlei
(ח) חָכְמַת עָרוּם הָבִין דַּרְכּוֹ 
וְאִוֶּלֶת כְּסִילִים מִרְמָה:
The wisdom of the shrewd man enables him to carefully consider his course of action and to understand his way — חָכְמַת עָרוּם הָבִין דַּרְכּוֹ ; the foolishness of fools is to use their cleverness for deceit — וְאִוֶּלֶת כְּסִילִים מִרְמָה .
Additional Insights
A series of insights illuminating this proverb are presented below. The numbers identifying the insights refer to the listing of sources at the end of the segment.
(1) The wise man uses shrewdness to weigh his options and determine the right way to go.
(2) The wise man uses his shrewdness to take control of events for good, whereas the fool uses shrewdness to take control of events for harm.
(3) Out of all the possible avenues of self-development, the wise man uses his shrewdness to refine his actions and behavior. In contrast, the fool chooses to develop the techniques of deception.
(4) The wise man uses shrewdness to develop a self-awareness of his status in worldly affairs and in knowledge relative to others. In this way he will know when to step forward and when to wthdraw in social situations.
(5) The wise man uses shrewdness to evaluate market conditions so that he can conduct a profitable business. In contrast the fool uses deception and underhanded practices to achieve his goals at the expense of others.
(6) The wise man is constantly examining his attitude and his behavior looking for faults within himself in order to improve his ways. In contrast the fool studies the faults of others, supposedly to learn how to avoid their shameful practices. The problem is that by exposing himself to disreputable behavior he ends up emulating it.
(7) The wise person needs to be shrewd in order to understand the subterfuges that the yetzer hara (evil nclination) is using to draw him into sinful behavior. In contrast the fool allows himself to become the victim of these deceptive techniques and instead of protecting himself, he draws others into the net.
Sources
The primary sources used for the additional insights illuminating this segment are listed below.
(1) – רש”י, אבן עזרא,
(2) – מצודות
(3) – רבינו יונה
(4) – המאירי
(5) – שבט מיהודה
(6) – חנוך לנער
(7) – הגר”א